PDF Summary:Be More Pirate, by Sam Conniff Allende

When we think about pirates, we usually picture brutal thieves, murderers, and rum lovers terrorizing the seas. In Be More Pirate, entrepreneur Sam Conniff offers a new perspective. He demonstrates how, during the Golden Age of Piracy from 1690 to 1725, pirates were innovators and disruptors who challenged an unjust political and economic order, made massive fortunes, and became legends. Conniff argues that our modern era of frequent conflict and growing inequality isn’t all that different from the one the Golden Age pirates inhabited—and that by adopting a pirate mindset, you too can find success and change the world.

Our guide to Be More Pirate will describe legendary pirates of old, their modern counterparts, and the tenets of the pirate mindset, so you too can go pirate and find success.

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Finding the Time and Place to Disrupt

If you really want your disruption to count, you have to act at the right time and place. In You Can Just Do Things, Jay Yang argues that you have to actively seek out these opportunities instead of hoping they’ll come. This means reaching out to others you think may be interested in your ideas and being wherever the action is, which might require moving or joining related online communities. To use Conniff’s example, in Apple’s early days, Steve Jobs ran the company out of his parents' home in the Bay Area—a burgeoning tech region—and spent hours on the phone seeking investors.

Decades later, Apple officials keeping a close eye on music piracy and storage software discovered a project made by two ex-Apple employees called SoundJam. Jobs rehired the ex-employees, and their software became iTunes.

Trait #2: Pirates Are Equal

The most disruptive ideas Golden Age Pirates had were often related to equality. This is why the second key pirate trait is egalitarianism, or treating everyone equally. Conniff explains that treating everyone equally is not only morally correct, but it’s also often the smart move for running a business or other group effort. When everyone feels like they have an equal say and will benefit equally from success, they’ll feel like they are part of a team. This will motivate them to work harder. In addition, when you treat people equally regardless of their background, you’ll often find overlooked talent and new perspectives you wouldn’t otherwise.

(Shortform note: One example of an egalitarian structure in workplaces is the participatory workplace, where decisions are made collectively by everyone they impact. Under this structure, a decision that only impacts one person—how they organize their desk, for example—can be made by that individual alone. But decisions that impact a greater number of people can only be made once everyone in that group has had a say. Even if someone is still in charge and the will of the group doesn’t always win out, this model still makes everyone feel like they have input into important matters.)

In a period of history with kings, slaves, and everyone in between, Golden Age Pirates were often far more egalitarian than their law-abiding counterparts. For example, the famous pirate captain Sam Bellamy, known as “Black Sam,” became a pirate in part to escape the harsh treatment of the British Navy. Then, when he had his own successful crew—by some accounts, it made the most money of any pirate crew in recorded history—he split his proceeds equally among everyone.

(Shortform note: Black Sam’s generosity became legendary not just because of how he treated his crew, but also because of how he treated his victims—with kindness and courtesy. For example, he once stole a ship and then gave its crew one of his old ships to sail home in.)

Most crews divided their loot equally, Conniff explains. They’d even set aside funds to pay out to injured crewmates. Golden Age Pirates also practiced a version of social equality and even democracy decades before any government. They accepted people from all kinds of backgrounds, regardless of social norms, including escaped slaves and women. They also organized their crews horizontally, often having more than one captain and voting on big decisions.

(Shortform note: Pirate democracy was just one example of a growing wave of democratic movements that emerged as friction grew between the public and Europe’s monarchies. Another example of a pro-democracy movement was the Diggers, a political and religious sect that emerged from the English Civil War in the mid-17th century. The Diggers were a peasant movement that believed in land redistribution to create rural, agricultural communities that shared wealth and made decisions collectively. Much like the Golden Age Pirates, the Diggers were eventually beaten by Europe’s powerful monarchies, their democratic ideas too soon for their era.)

Practicing Equality

Conniff argues that you can practice pirate equality in your own life by sharing your power with the people who help you along the way. In a group setting, power sharing can mean openly sharing your knowledge with others, delegating tasks to them, and letting them pursue those tasks independently—giving them the power to do their jobs. Conniff notes that you should also delegate and recruit people from a wide variety of backgrounds whenever possible, and treat anyone “below” you with respect.

(Shortform note: The authors of Humanocracy emphasize the role of personal connection in the process of sharing power with the people under you. They explain that you should avoid getting lost in layers of strict rules and systems that treat people like items on a spreadsheet. Instead, get to know the people under you and their strengths. This will help you delegate more effectively and also show them that you respect them enough to take an interest in them.)

Conniff also recommends sharing your success with others. This can mean different things depending on what success looks like. It means fair compensation in a business context, but elsewhere, it might mean finding ways to show your appreciation. For example, if you win a promotion at work, you might treat your partner and close friends to dinner to express gratitude for their support.

For an example of modern-day pirate equality, Conniff tells the story of hip-hop artist RZA, who belongs to the group the Wu-Tang Clan. Despite having almost no money at the start of his career, RZA rejected any record deal that would restrict who he and the other Wu-Tang artists could sign with. And when the Wu-Tang Clan eventually went platinum and found major success, RZA helped each of its members get their own album deals as individual artists and created a system where they all shared the revenue from their records.

(Shortform note: Sharing success can be important not only because of the benefits it brings but also because of the negative consequences it prevents. Hip hop group N.W.A. provides a contrasting example with the Wu-Tang Clan, illustrating how failing to share success can destroy it. The group started to fall apart in 1989 over royalty and contract disputes, with various members disagreeing about who wrote what and how much they should be compensated for their work. This not only led the group to collapse but also started a bitter feud between its former members that lasted for years.)

Trait #3: Pirates Are Practical

Conniff explains that while it’s easy to get caught up in the idealism of pirate disruption and equality, you need to stay practical—prioritize pursuing realistic solutions to immediate problems. When you’re focused on your immediate problems, you think in terms of what you have and what you need first. You’re also able to approach problems more flexibly, since you’re committed to doing whatever works best for each specific problem instead of getting tunnel vision on an idea of how things “should” be done.

(Shortform note: To focus on your most pressing problems, you have to know how to prioritize them. Mike Michalowicz (Fix This Next) argues that you have to focus on problems related to your vital need—whatever your organization can’t survive without. Once you’ve solved the problems related to immediate survival (or you’ve at least prevented major catastrophes), you can focus on the problems that prevent longer-term stability, and then the longer-term projects that can improve the way your organization runs. While Michalowicz is specifically referring to entrepreneurship, the same techniques can apply to your personal life as well.)

Conniff explains that Golden Age Pirates were practical out of necessity—they were much fewer, poorer, and less powerful than the massive empires and corporations they stole from. They chose to be disruptive and equal not out of idealism but to address specific, personal problems in their lives—escaping an exploitative job, coordinating a group of disparate outcasts, and so on. They were also willing to be flexible with these tenets when necessary. For example, during a fight or other dangerous situation, pirate crews could temporarily set aside their horizontal structure and put a captain in charge. This ensured that crews had both the benefits of equality and the ability to get everyone on the same page during an emergency.

(Shortform note: Golden Age pirate practicality didn’t just bring individual members of a crew together, but it also contributed to a sense of camaraderie between disparate pirate crews. Knowing they were out-gunned and had few friends at sea, pirate crews often made alliances or helped each other whenever they met on the high seas. This cooperation wasn’t just about shared ideals—there was practical value in not having to worry about infighting and backstabbing, allowing crews to focus on the common threat of the law. Working together and sharing resources also meant crews in need could receive help.)

Practicing Practicality

To adopt pirate practicality in your own life, Conniff recommends you start by questioning your plans for your business, career, or life. Ask yourself if you’re following this path because it’s best for you or because that’s what people say you’re supposed to do. Consider some alternatives to this path that address whatever you truly need.

As an example, Conniff discusses the business dogma of always pursuing exponential growth. Companies often follow this dogma even if it decreases product quality, increases financial risk, or leads to unethical dealings. However, a company could avoid these consequences by rejecting the dogma of exponential growth and pursuing a plan that suits its business model and place in the industry.

(Shortform note: Sometimes, the best alternative path is doing nothing at all. Celeste Headlee (Do Nothing) argues that people often feel pressured to be as productive and efficient as possible—a dogmatic belief that harms both your personal and professional life through burnout and increased stress. Headlee recommends you challenge this belief by ensuring you find time to spend on leisure or pleasure for its own sake. Not only will this help you feel better, but it’ll also have the practical benefit of energizing you when it’s time to get back to work.)

Trait #4: Pirates Are Storytellers

The fourth and final pirate trait Conniff discusses is storytelling—or rather, the pirate version of storytelling, which involves committing to your ideas and being unafraid to challenge people with them. He explains that for an idea to really stick, you have to provoke a strong emotional reaction in your audience. You won’t cause these responses through partial commitment, or by only speaking to people who you know agree with you. Instead, you must be willing to test your ideas with potentially unfriendly audiences and be willing to make people uncomfortable.

(Shortform note: Lisa Cron (Wired for Story) explains the neurology behind why stories stick when they evoke strong emotions: Our brains use emotions to determine what information is important. If a piece of information doesn’t make you feel anything, your brain considers it unimportant. But if it provokes a strong emotional reaction, your brain will take note of that and put more effort into retaining the information. So, if your pirate-esque ideas make people feel uncomfortable emotions—or make them feel seen in a way they’re unaccustomed to, because more traditional ways of thinking don’t resonate with them—they’ll be more likely to remember them.)

Conniff explains that pirates were incredible storytellers. They created the first international brand with the Jolly Roger, a black and white skull-and-crossbones flag flown by all pirate ships. During the Golden Age, the Jolly Roger was instantly recognizable to any naval or merchant vessel, and it terrified them.

The best Golden Age storyteller of all was the legendary pirate Edward Teach, better known as Blackbeard—a man so good at convincing people he was dangerous that he rarely had to fight. A master of intimidation, he’d tie lit fuses into his massive, dark beard so he was wreathed in smoke and flame, wore all black, and had a habit of randomly firing his pistol in the air just to keep people scared of him. Blackbeard even made under-the-table deals with colonial governors, privately cooperating with them while they publicly reinforced his reputation as a vicious killer. This method worked wonders for him—some historians argue that Blackbeard never even had to kill anyone, because he was so terrifying that everyone he went after surrendered without a fight.

Golden Age Pirate Legends

Golden Age pirates had help inflating their achievements and spreading their stories. Journalists and novelists of the era also discovered that audiences abroad wanted to read about pirates—the grislier the details, the better. To sell more books and newspapers, authors and editors frequently added their own made-up details to make existing stories more exciting.

Blackbeard’s legacy grew with the 1724 publication of Charles Johnson’s A General History of the Pirates, a biography of Golden Age pirates that sold incredibly well. Johnson’s work also had the first-ever written description of the Jolly Roger, further boosting the symbol’s infamy. This public fascination and industry of pirate stories are a big part of why pirates are legendary to this day.

Practicing Storytelling

Chances are, you’re not trying to convince your potential audience that you’re a vicious killer. Nor do you want to make them actively uncomfortable and upset. But Conniff explains that you can still embrace pirate storytelling with three main techniques: First, find your own Jolly Roger—the simple, specific image or concept that represents your idea. Second, find the emotional core of the story you want to tell and focus on it above everything else. Finally, don’t get tunnel vision on who you think wants to hear your story or worry too much about who will like it. Be willing to take risks and bring your ideas to new places.

(Shortform note: Matthew Dicks (Storyworthy) elaborates further on how to find your story’s emotional core. He explains that the best stories center around moments of personal transformation—moments where you gain insight that changes the way you think or feel about something. People like stories that feel authentic, and personal transformations cause your audience to reflect. Making your story about a small, personal moment also makes it more likely to relate to a larger audience, meaning you can worry less about a specific ideal audience. For example, you could tell a story about how you were angry at traffic during your commute, only to realize that you were actually angry about feeling stuck in your career.)

Conniff’s modern example of a pirate storyteller is blues pianist Daryl Davis. Davis, a Black American, devoted years of his life to befriending members of the Ku Klux Klan and convincing them to leave the hate group. Instead of running away, Davis listened to stories about their lives and talked about his own—presenting himself as a real person and developing a friendship with them. And while he challenged their ideas, he did so calmly and politely until their worldviews eventually fell apart.

(Shortform note: Davis’s strategy of stopping hatred through storytelling can even work on a national level. After the fall of South Africa’s white supremacist apartheid regime, the Truth and Reconciliation Commission (TRC) asked victims and perpetrators of the regime’s human rights abuses to come forward and tell their stories. Perpetrators who told the full truth were often granted amnesty in exchange. The TRC, along with other measures like reparations, was considered by many to be an important step in the national healing process.)

Part 4: Developing a Pirate Code

Conniff explains that to fully embrace the pirate life, you need a pirate code. In the Golden Age, these codes were the rules each crew lived by. They were living documents, constantly being updated, but still provided an overall vision and way of life. By creating your own pirate code, you can organize your own goals, values, and plans moving forward. No matter how complicated things get in practice, you’ll always have the code to refer back to when you need to remind yourself of the core values of your organization.

(Shortform note: The authors of Life Worth Living elaborate further on the value of a code or life philosophy, arguing that it helps you live more intentionally. They argue that when people lack a code, they tend to make big decisions based on instinct, often leading to poor decisions. But a life philosophy provides you with a list of the values and beliefs that matter most to you, which you can reference when making big decisions. This ensures your decision will be better informed.)

Let’s explore Golden Age pirate codes and Conniff’s advice for creating your own.

Black Bart’s Pirate Code

The codes of Golden Age pirates included plenty of administrative and logistical rules, but Conniff focuses on their core tenets to provide an example of what a pirate code looks like. Specifically, let’s examine the code of Golden Age pirate Black Bart—arguably the most successful pirate of all time, he captured over 400 ships in his brief, three-year career.

Here are a few key points of Black Bart’s code:

1) Everyone gets a vote on major decisions and equal access to food and liquor unless rationing is necessary.

2) Everyone gets their fair share of loot—officers get a bit more, but no more than double shares—and is punished for hoarding more. Anyone injured gets a payout depending on the severity of their wound.

3) No gambling and no women on board, punishable by execution. (Conniff explains this was partially to prevent women from being taken captive and mistreated.)

This code kept the crew organized, held them accountable for their responsibilities, and enshrined their rights as pirates. In other words, it was the rulebook for what it meant to be aboard Black Bart’s ship.

(Shortform note: Crewmembers didn’t just follow their pirate codes because of equality and democracy—they also did so because the punishment for breaking rules was often brutal. While pirates tried to avoid fights with their victims and other crews, they weren’t afraid to use violence on rulebreakers within their crews to maintain order. Pirates who broke the code were often tortured, executed, or marooned—kicked off the crew and left on a deserted island or other inaccessible locale. This suggests that fear of violence, along with equality, kept pirates in line.)

Black Bart’s Code

Historians explain that Black Bart’s code contributed to his incredibly successful career by keeping his men disciplined and professional. Bans on gambling, women, theft, and duels on board gave crew members fewer things to fight over and provided rules for conflicts that did arise. Meanwhile, other rules, like keeping pistols maintained and turning all lights out at eight o’clock, meant everyone would be alert and ready whenever trouble arose. Finally, Bart’s democratic measures gave crewmembers good reasons to keep cooperating and following the rules—they had an excellent gig and didn’t want to mess it up.

This discipline and professionalism meant Roberts could trust his men to commit to and pull off daring maneuvers, like when he stealthily joined a Portuguese treasure fleet, discovered which ship had the most loot, robbed it, and then sailed away before the fleet’s escort was even aware of what had happened.

Creating Your Own Pirate Code

Conniff provides two methods you can use to create your own pirate code; let’s explore each.

Method #1: Take Other People’s Good Ideas

Whether they come from other businesses in your industry, people you personally respect, or Golden Age Pirates, you should take any good ideas you find and add them to your code. Conniff emphasizes searching for strategies that are working well in the present—remember, pirates are practical.

(Shortform note: Before you can take other people’s good ideas, you have to find them first. Artist Austin Kleon (Steal Like an Artist) recommends you curate your sources of inspiration: Start with a deep dive into the ideas or work of one person that you want to learn from, and then learn about the people or ideas that inspired them. This gives you a baseline of ideas you can build off of, pursuing whatever interests or excites you most.)

Method #2: Focus on What You Love

The second method of creating a pirate code that Conniff recommends involves getting to know yourself on a deeper level. Ask yourself what matters most to you—the projects and values you’d gladly devote your life to. Once you have a better sense of what you really care about, this can inform your pirate code. Conniff also recommends pushing past the normal reasons why you might stop yourself from pursuing these goals, as doubt will only keep you in whatever status quo is making you dissatisfied.

(Shortform note: To find what it is you love and care about, life coach Mike Bayer (Best Self) suggests you take stock of six parts of your life: your relationship with yourself,your relationships with others, your physical health, your hobbies and skills, your career, and your faith. If one of these areas makes you uncomfortable or unsatisfied, that’s a good indication that you need a change. And if there are specific parts that are comforting or give you a lot of satisfaction—a specific relationship, a hobby, and so on—then consider why. The answer will provide you with insight into what matters to you.)